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From salts to ionic liquids by systematic structural modifications: A rational approach towards the efficient modular synthesis of enantiopure imidazolium salts

This paper reports a simple and robust modular synthetic strategy that leads to a large variety of configu- rationally and structurally diverse imi- dazole-based chiral ionic liquids (CILs) by lipase-catalyzed resolution. The intimate microscopic interactions of the supramolecular ionic network of these imidazolium chiral salts at the molecular level are investigated both spectro- scopically (NMR, FT-IR-ATR) and theoretically, and a topological analysis of the experimental electron densities obtained by X-ray diffraction of single crystals is performed. Our results support the key role played by the relative configuration of the -OR group on the hydrogen-bonding pattern and its strong influence on the final physical properties of the imidazolium salt. We also obtained a reasonable correlation between the observed melting point and the non-covalent interactions. The spectroscopic data and the topological analysis reflect the key role played by hydrogen bonds between the OH and imidazolium C2H groups in both cation-anion and cation-cation interactions, with the presence of an OH group leading to an additional inter-cation interaction. This interaction sig- nificantly affects the properties of ste- reoisomeric salts. Even more interestingly, we also studied the effect of the chirality by comparing enantiopure CILs with their racemic mixtures and found that, with the exception of trans- Cy6-OH-Im-Bn-Br, the melting points of the racemic mixtures are higher than those of the corresponding enantiomer- ically pure forms. For stereoisomeric examples, we have successfully explained the differences in melting temperatures in light of the corresponding structural data. Chirality should therefore be taken into account as a highly attractive design vector in the preparation of ILs with specifically desired properties.

Simple and straightforward synthesis of novel enantiopure ionic liquids via efficient enzymatic resolution of (±)-2-(1H-imidazol-1-yl)cyclohexanol

Both enantiomers of enantiopure imidazolium ionic liquids were synthesized by a simple and straightforward procedure from (R,R)- and (S,S)-2-(1H-imidazol-1-yl)cyclohexanol derivatives obtained via lipase-catalyzed resolution. Structural properties and the